AP492A - 1,5 Benzodiazepine derivatives. - Google Patents
1,5 Benzodiazepine derivatives. Download PDFInfo
- Publication number
- AP492A AP492A APAP/P/1994/000657A AP9400657A AP492A AP 492 A AP492 A AP 492A AP 9400657 A AP9400657 A AP 9400657A AP 492 A AP492 A AP 492A
- Authority
- AP
- ARIPO
- Prior art keywords
- dioxo
- benzodiazepin
- ethyl
- compounds
- formula
- Prior art date
Links
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 224
- -1 hydroxy, phenyl Chemical group 0.000 claims description 115
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 108010052343 Gastrins Proteins 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 230000008901 benefit Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 102100021022 Gastrin Human genes 0.000 claims 2
- IQZBVVPYTDHTIP-UHFFFAOYSA-N (4-fluorophenyl)urea Chemical compound NC(=O)NC1=CC=C(F)C=C1 IQZBVVPYTDHTIP-UHFFFAOYSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- LPGHVRUYPHPZBN-UHFFFAOYSA-N 1-[5-[2-(dimethylamino)ethyl]-1-(3-methylbutyl)-2,4-dioxo-1,5-benzodiazepin-3-yl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1C(=O)N(CCN(C)C)C2=CC=CC=C2N(CCC(C)C)C1=O LPGHVRUYPHPZBN-UHFFFAOYSA-N 0.000 claims 1
- ZLYQBVDEPMBDMC-UHFFFAOYSA-N 1-[5-[2-(dimethylamino)ethyl]-1-(3-methylbutyl)-2,4-dioxo-1,5-benzodiazepin-3-yl]-3-phenylurea Chemical compound O=C1N(CCC(C)C)C2=CC=CC=C2N(CCN(C)C)C(=O)C1NC(=O)NC1=CC=CC=C1 ZLYQBVDEPMBDMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
- 239000000243 solution Substances 0.000 description 146
- 239000000543 intermediate Substances 0.000 description 125
- 239000000203 mixture Substances 0.000 description 103
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- 239000007787 solid Substances 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
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- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000012299 nitrogen atmosphere Substances 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 101710089098 Cholecystokinins Proteins 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000006260 foam Substances 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229960004132 diethyl ether Drugs 0.000 description 17
- 239000000725 suspension Substances 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 15
- 229940049706 benzodiazepine Drugs 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- 150000003141 primary amines Chemical class 0.000 description 14
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 11
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- DVARZUUKZACNGW-UHFFFAOYSA-N 2-(phenylhydrazinylidene)propanedioyl dichloride Chemical compound ClC(=O)C(C(Cl)=O)=NNC1=CC=CC=C1 DVARZUUKZACNGW-UHFFFAOYSA-N 0.000 description 9
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 9
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 8
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
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- Neurology (AREA)
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- Pain & Pain Management (AREA)
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- Diabetes (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939314981A GB9314981D0 (en) | 1993-07-20 | 1993-07-20 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9400657A0 AP9400657A0 (en) | 1994-07-31 |
| AP492A true AP492A (en) | 1996-05-13 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| APAP/P/1994/000657A AP492A (en) | 1993-07-20 | 1994-07-18 | 1,5 Benzodiazepine derivatives. |
Country Status (32)
| Country | Link |
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| US (1) | US5716953A (en, 2012) |
| EP (1) | EP0710230B1 (en, 2012) |
| JP (1) | JP3587849B2 (en, 2012) |
| KR (1) | KR100347287B1 (en, 2012) |
| CN (1) | CN1050835C (en, 2012) |
| AP (1) | AP492A (en, 2012) |
| AT (1) | ATE171167T1 (en, 2012) |
| AU (1) | AU687858B2 (en, 2012) |
| CA (1) | CA2167308A1 (en, 2012) |
| CO (1) | CO4290299A1 (en, 2012) |
| CZ (1) | CZ290472B6 (en, 2012) |
| DE (1) | DE69413405T2 (en, 2012) |
| DK (1) | DK0710230T3 (en, 2012) |
| EC (1) | ECSP941120A (en, 2012) |
| ES (1) | ES2123812T3 (en, 2012) |
| FI (1) | FI960223A7 (en, 2012) |
| GB (1) | GB9314981D0 (en, 2012) |
| HR (1) | HRP940411B1 (en, 2012) |
| HU (1) | HU222439B1 (en, 2012) |
| IL (1) | IL110366A (en, 2012) |
| IS (1) | IS4190A (en, 2012) |
| MY (1) | MY118638A (en, 2012) |
| NO (1) | NO313288B1 (en, 2012) |
| NZ (1) | NZ271075A (en, 2012) |
| PE (1) | PE8295A1 (en, 2012) |
| PL (1) | PL175609B1 (en, 2012) |
| RU (1) | RU2135485C1 (en, 2012) |
| SI (1) | SI0710230T1 (en, 2012) |
| SV (1) | SV1994000031A (en, 2012) |
| TW (1) | TW290542B (en, 2012) |
| WO (1) | WO1995003285A1 (en, 2012) |
| ZA (1) | ZA945238B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5739129A (en) * | 1994-04-14 | 1998-04-14 | Glaxo Wellcome Inc. | CCK or gastrin modulating 5-heterocyclic-1, 5 benzodiazepines |
| PE27497A1 (es) * | 1994-04-15 | 1997-08-07 | Glaxo Inc | Derivados de 1,5 benzodiazepina |
| AU3459497A (en) * | 1996-07-12 | 1998-02-09 | Chugai Seiyaku Kabushiki Kaisha | Cancer cell proliferation inhibitors |
| US6683075B1 (en) | 1996-12-23 | 2004-01-27 | Athena Neurosciences, Inc. | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use |
| US6635632B1 (en) | 1996-12-23 | 2003-10-21 | Athena Neurosciences, Inc. | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| US20030190307A1 (en) | 1996-12-24 | 2003-10-09 | Biogen, Inc. | Stable liquid interferon formulations |
| US6569851B1 (en) * | 1998-06-22 | 2003-05-27 | Elan Pharmaceutials, Inc. | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| US6958330B1 (en) | 1998-06-22 | 2005-10-25 | Elan Pharmaceuticals, Inc. | Polycyclic α-amino-ε-caprolactams and related compounds |
| WO2001029012A2 (en) | 1999-10-15 | 2001-04-26 | F. Hoffmann-La Roche Ag | Benzodiazepine derivatives as metabotropic glutamate receptor antagonists |
| US20050192265A1 (en) * | 2003-03-20 | 2005-09-01 | Thompson Richard C. | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds |
| CA2541470C (en) * | 2003-10-06 | 2011-11-29 | F.Hoffmann-La Roche Ag | Substituted dibenzo-azepine and benzo-diazepine derivatives useful as gamma-secretase inhibitors |
| CA2557657C (en) * | 2004-02-27 | 2013-06-18 | Aortx, Inc. | Prosthetic heart valve delivery systems and methods |
| EP2137167B1 (en) * | 2007-04-19 | 2011-08-10 | F. Hoffmann-La Roche AG | Dihydro-benzo[b][1,4]diazepin-2-one sulfonamide derivatives |
| RU2540464C2 (ru) * | 2012-05-28 | 2015-02-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный медицинский университет" Министерства здравоохранения и социального развития Российской Федерации | Водорастворимое производное амида салициловой кислоты, обладающее транквилизирующей, ноотропной и анальгезирующей активностью |
| CN103435562B (zh) * | 2013-08-26 | 2016-02-24 | 华东理工大学 | 6-取代苯并二氮卓-2,4-二酮类化合物及其用途 |
| RU2702359C1 (ru) * | 2019-06-04 | 2019-10-08 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,2,4-триалкил-2,3-дигидро-1Н-1,5-бензодиазепинов |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0376849A1 (fr) * | 1988-12-29 | 1990-07-04 | Roussel-Uclaf | Nouveaux dérivés de la 2,4-dioxo 2,3,4,5-tétrahydro 1H-1,5-benzodiazépine, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant |
| EP0514133A1 (en) * | 1991-05-14 | 1992-11-19 | MERCK SHARP & DOHME LTD. | Benzodiazepine derivatives, compositions containing them and their use in therapy |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2103745A1 (de) * | 1971-01-27 | 1972-08-10 | CH. Boehringer Sohn, 6507 Ingelheim | Neue 5-AryJ-(bzw. Heteroaryl)-3-hydroxylH-l,5-benzodiazepin-2,4-(3H,5H)-dioneund Verfahren zu ihrer Herstellung |
| GB9201180D0 (en) * | 1992-01-21 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
| GB9201181D0 (en) * | 1992-01-21 | 1992-03-11 | Glaxo Spa | Chemical compounds |
| GB9225492D0 (en) * | 1992-12-05 | 1993-01-27 | Glaxo Group Ltd | Amine derivatives |
-
1993
- 1993-07-20 GB GB939314981A patent/GB9314981D0/en active Pending
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1994
- 1994-07-15 IS IS4190A patent/IS4190A/is unknown
- 1994-07-18 KR KR1019960700279A patent/KR100347287B1/ko not_active Expired - Fee Related
- 1994-07-18 RU RU96102670A patent/RU2135485C1/ru not_active IP Right Cessation
- 1994-07-18 SI SI9430207T patent/SI0710230T1/xx not_active IP Right Cessation
- 1994-07-18 CN CN94193283A patent/CN1050835C/zh not_active Expired - Fee Related
- 1994-07-18 PE PE1994246888A patent/PE8295A1/es not_active Application Discontinuation
- 1994-07-18 ZA ZA945238A patent/ZA945238B/xx unknown
- 1994-07-18 EP EP94924257A patent/EP0710230B1/en not_active Expired - Lifetime
- 1994-07-18 AU AU74589/94A patent/AU687858B2/en not_active Ceased
- 1994-07-18 CZ CZ1996173A patent/CZ290472B6/cs not_active IP Right Cessation
- 1994-07-18 MY MYPI94001865A patent/MY118638A/en unknown
- 1994-07-18 WO PCT/EP1994/002353 patent/WO1995003285A1/en active IP Right Grant
- 1994-07-18 HU HU9600124A patent/HU222439B1/hu not_active IP Right Cessation
- 1994-07-18 DK DK94924257T patent/DK0710230T3/da active
- 1994-07-18 JP JP50492695A patent/JP3587849B2/ja not_active Expired - Fee Related
- 1994-07-18 HR HR940411A patent/HRP940411B1/xx not_active IP Right Cessation
- 1994-07-18 ES ES94924257T patent/ES2123812T3/es not_active Expired - Lifetime
- 1994-07-18 CO CO94031454A patent/CO4290299A1/es unknown
- 1994-07-18 US US08/578,535 patent/US5716953A/en not_active Expired - Fee Related
- 1994-07-18 EC EC1994001120A patent/ECSP941120A/es unknown
- 1994-07-18 CA CA002167308A patent/CA2167308A1/en not_active Abandoned
- 1994-07-18 AT AT94924257T patent/ATE171167T1/de not_active IP Right Cessation
- 1994-07-18 AP APAP/P/1994/000657A patent/AP492A/en active
- 1994-07-18 NZ NZ271075A patent/NZ271075A/en unknown
- 1994-07-18 DE DE69413405T patent/DE69413405T2/de not_active Expired - Fee Related
- 1994-07-18 PL PL94312659A patent/PL175609B1/pl not_active IP Right Cessation
- 1994-07-19 IL IL11036694A patent/IL110366A/en not_active IP Right Cessation
- 1994-07-19 SV SV1994000031A patent/SV1994000031A/es active IP Right Grant
- 1994-07-22 TW TW083106738A patent/TW290542B/zh active
-
1996
- 1996-01-17 FI FI960223A patent/FI960223A7/fi unknown
- 1996-01-19 NO NO19960237A patent/NO313288B1/no unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0376849A1 (fr) * | 1988-12-29 | 1990-07-04 | Roussel-Uclaf | Nouveaux dérivés de la 2,4-dioxo 2,3,4,5-tétrahydro 1H-1,5-benzodiazépine, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant |
| EP0514133A1 (en) * | 1991-05-14 | 1992-11-19 | MERCK SHARP & DOHME LTD. | Benzodiazepine derivatives, compositions containing them and their use in therapy |
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